Acetyl chloride → HCID 46913466, compound

HRID 1626551Notes

Reaction equation

HRID 1626551 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:16]3[CH2:21][NH:20][CH2:19][C:17]=3[N:18]=2)=[CH:9][CH:8]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:20]1[CH2:21][C:16]2[C:15]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])=[N:14][C:13]([C:10]3[CH:11]=[CH:12][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[CH:8][CH:9]=3)=[N:18][C:17]=2[CH2:19]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 46913468HCID 46913468, compound

Product 1

HCID 46913466HCID 46913466, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-ethyl-3-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl)urea (example 7) (60 mg, 0.16 mmol) in DCM (1.5 mL) was added triethylamine (42 uL, 0.31 mmol) and acetyl chloride (71 uL, 0.31 mmol). The reaction mixture was stirred overnight at room temperature, concentrated in vacuo, then diluted with water and ethyl acetate. The organic layer was concentrated and purified by prep HPLC (low pH) to give an off-white solid (5.7 mg, 0.013 mmol, 9% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-f82a7cfe679a484884ab86068a3471de
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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